4-Methylcyclohexanemethanol
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4-Methylcyclohexanemethanol
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CAS No:
34885-03-5
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Formula:
C8H16O
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Chemical Name:
4-Methylcyclohexanemethanol
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Synonyms:
Cyclohexanemethanol,4-methyl-;4-Methylcyclohexanemethanol;Hexahydro-p-methylbenzyl alcohol;(4-Methylcyclohexyl)methanol;4-Methylcyclohexane methanol;1-(4-Methylcyclohexyl)methanol
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CAS No:
Description
Liquid
4-methylcyclohexanemethanol is an alicyclic primary alcohol that is cyclohexane substituted by a hydroxy methyl group and methyl group at positions 1 and 4. It acts as a hydrotrope, solubilizing hydrophobic substances in aqueous environments. It also prevents protein aggregation, alters membrane dynamics and metal homeostasis, and is used in a flotation process for cleaning and processing coal. It is an aliphatic alcohol, a primary alcohol and a carbocyclic compound.
4-Methylcyclohexanemethanol Basic Attributes
128.21
128.21
609-038-8
64PJK2GTXA|9TEH6BZ70K
DTXSID9041813|DTXSID80274141|DTXSID40274142
Clear, colorless liquid
2906199090
Characteristics
20.23000
1.80500
1.0176 g/cm3 @ Temp: 20 °C
202 °C
80.2ºC
1.4610 to 1.4640
In water, 2.024X10+3 mg/L at 25 °C (est)
Store away from incompatible materials such as oxidizing agents.|Keep container tightly closed. Store in a cool, dark and well-ventilated place.
5.8X10-2 mm Hg at 25 °C (est)
Almost odorless|Alcohol|As a class of organic alcohols, it has an obvious odor and is reported to smell like licorice. /Crude MCHM/
15.05±0.10
Henry's Law constant = 6.43X10-6 atm-cu m/mol at 25 °C (est)
Hydroxyl radical reaction rate constant = 1.65X10-11 cu cm/molec-sec at 25 °C (est)
Safety Information
36/37/38
26-36/37/39
Stable under proper conditions.
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.
Oxidizing agents
West Virginia Poison Center and Mid-Atlantic Center for Children's Health & the Environment; Factsheet February 10, 2014.[West Virginia Poison Center and Mid-Atlantic Center for Children's Health & the Environment; Factsheet February 10, 2014; Available from, as of April 3, 2014: http://childrensnational.org/~/media/cnhs-site/files/research-and-education/partners-collaborators/macche/charleston_wv_health_professionals_factsheet.ashx?la=en]|CDC: Summary Report of Short-term Screening Level Calculation and Analysis of Available Animal Studies for MCHM[CDC: Summary Report of Short-term Screening Level Calculation and Analysis of Available Animal Studies for MCHM; Available from, as of March 6, 2014: http://emergency.cdc.gov/chemical/MCHM/westvirginia2014/pdf/MCHM-Summary-Report.pdf]|U.S. Chemical Safety Board; Freedom Industries Chemical Release. Accident Description: A leak originating from a storage tank at Freedom Industries contaminated the local water supply leaving hundreds of thousands of West Virginia residents without clean drinking water. The CSB's investigation is currently ongoing. No related Recommendations found.[U.S. Chemical Safety Board; Freedom Industries Chemical Release. Available from, as of July 17, 2014: http://www.csb.gov/freedom-industries-chemical-release-/]|HHS/NTP; West Virginia Chemical Spill: NTP Research Response Fact Sheet (August 2014).[Available from, as of September 18, 2014: http://www.niehs.nih.gov/health/materials/west_virginia_chemical_spill_ntp_research_response_508.pdf]|For more Special Reports (Complete) data for 4-Methylcyclohexanemethanol (6 total), please visit the HSDB record page.
Protective clothing. Protective boots, if the situation requires.|Safety glasses. A face-shield, if the situation requires.|Protective gloves.|Vapor respirator.|Use personal protective equipment. Keep people away from and upwind of spill/leak. Ensure adequate ventilation. Entry to non-involved personnel should be controlled around the leakage area by roping off...
When extinguishing fire, be sure to wear personal protective equipment.|Fire-extinguishing work is done from the windward and the suitable fire-extinguishing method according to the surrounding situation is used. Uninvolved persons should evacuate to a safe place. In case of fire in the surroundings: Remove movable containers if safe to do so.|Dry chemical, foam, water spray, carbon dioxide.
Prevent product from entering drains.|Absorb spilled material in a suitable absorbent (e.g. rag, dry sand, earth, saw-dust). In case of large amount of spillage, contain a spill by bunding. Adhered or collected material should be promptly disposed of, in accordance with appropriate laws and regulations.
Remove all sources of ignition. Fire-extinguishing devices should be prepared in case of a fire. Use sparkproof tools and explosion-proof equipment.|Install a closed system or local exhaust as possible so that workers should not be exposed directly. Also install safety shower and eye bath.|Use personal protective equipment. Keep people away from and upwind of spill/leak. Ensure adequate ventilation. Entry to non-involved personnel should be controlled around the leakage area by roping off...|Avoid contact with skin, eyes and clothing.|For more Preventive Measures (Complete) data for 4-Methylcyclohexanemethanol (7 total), please visit the HSDB record page.
A strong skin irritant|A moderate eye irritant
Toxicity
IDENTIFICATION AND USE: 4-Methylcyclohexanemethanol (MCHM) is a clear, colorless liquid, which is reported to smell like licorice. It is used in a coal industry in the separation of usable coal from rocks, debris and cold dust. HUMAN EXPOSURE AND TOXICITY: Symptoms of MCHM exposure include: nausea, vomiting, dizziness, headaches, diarrhea, reddened skin, itching, and rashes. In the days immediately following January 9, 2014, the West Virginia Poison Center received calls from over 1,900 patients reporting chemical exposures related to the drinking water. Most reported symptoms included mild rashes and reddened skin from dermal exposure, or GI distress (nausea, vomiting and/or diarrhea) from ingesting contaminated water. The symptoms tended to be mild and self-limiting. It was possible that the symptoms reported to be caused by exposure to MCHM could have been caused by other mild clinical illness such as colds or flu or other viral infections. Results of laboratory tests done in the Emergency Department did not indicate any people had new kidney or liver damage. With human A549 cells, MCHM mainly induced DNA damage-related biomarkers. ANIMAL STUDIES: Rats dosed with 800 mg/kg of MCHM showed signs of CNS depression resulting in decreased activity levels and ataxia. Administration of 400 mg/kg/day of the test article to rats by gavage for four weeks was associated with erythropoietic, kidney, and liver effects. The no-observed-effect level for this subacute toxicity study was 100 mg/kg/day. MCHM was a strong skin irritant in guinea pigs and moderate eye irritant in rabbits. NTP mouse study found MCHM is a skin irritant; however, it did not induce hypersensitivity unlike crude MCHM. An acute dermal toxicity study was conducted in male and female rats administered a single limit dose of 2000 mg/kg of the test substance topically. Two female rats died (on Day 1 and Day 3); the cause of death was not determined. For female rats, clinical sign observed included prostration, stumbling, transient weakness, and skin abnormalities (erythema, desquamation, and induration). Additionally, lack of feces, red urine, and inguinal hair wet with urine was observed for the female rats. For male rats, clinical signs observed were limited to erythema and desquamation of the skin at the site of application. All animals which survived to scheduled necropsy gained weight during the study. Treatment-related gross or microscopic changes were observed only for female rats. For the two female rats which died, treatment-related gross lesions included distention of the urinary bladder with red urine, and/or hemorrhage in the glandular gastric mucosa; darker than normal spleens were also observed in these rats. The lesions observed in the glandular gastric mucosa may have been due to consumption of test substance during grooming or may have been due to stress. Microscopic lesions consisted of atrophy and congestion of the splenic red pulp and/or atrophy and necrosis of the splenic white pulp. The white pulp atrophy may have been secondary to stress and the red pulp atrophy and congestion may have been related to stress and/or hemorrhage. In addition, splenic effects have not been associated with wrapping, and therefore, may be associated with test substance toxicity. Treatment-related lesions observed for one of the female rats that survived the 14-day observation period consisted of desquamation and minor induration of the skin at the application site grossly and consisted of focal necrosis and eschar formation on the skin at the application site microscopically. The test substance was a dermal irritant as evidenced by focal necrosis and eschar formation on the skin at the application site. In prenatal developmental toxicity study in rats NTP found that MCHM decreased fetal weight and induced malformations in fetuses (400 mg/kg/day). A small decrease in fetal weight was also observed (200 mg/kg/day). In zebrafish studies, MCMH did not have effects on embryonic and larval development and behavior, but it affected zebrafish photomotor response. In the yeast library, MCHM induced chemical stress related to transmembrane transport and transporter activity, while MCHM metabolites induced oxidative stress related to antioxidant activity and oxidoreductase activity. In the mutagenicity study with Salmonella typhimurium TA98, TA100, TA1535, TA1537, and Escherichia coli WP2uvrA (pKM101) MCHM was not active with or without metabolic activation. MCHM was negative in the in vivo rat micronucleus assay conducted by NTP. ECOTOXICITY STUDIES: LC50; Fathead minnow; Conditions: freshwater, static; Concentration 54.7 mg/L for 96 hr. EC50; Species: Daphnia magna (Water flea); Conditions: freshwater, static; Concentration: 98.1 mg/L for 48 hr; effect: stress and immobility. Others reported EC50 for Daphnia magna approximately 50 mg/L for 48 hr.
LD50 Rats dermal 3.6 mL/kg|LD50 Rats female oral 884 mg/kg|LD50 Rats male oral 1768 mg/kg|LD50 Rats dermal >2000 mg/kg|For more Non-Human Toxicity Values (Complete) data for 4-Methylcyclohexanemethanol (7 total), please visit the HSDB record page.
To ensure that the dams receive sufficient doses of MCHM in the prenatal toxicity study, a range-finding study was conducted. This study identified the dose that would be expected to result in minimal maternal toxicity. MCHM was mixed in corn oil vehicle and dose levels of 0 (controls), 150, 300, 600, and 900 mg/kg/day of MCHM were administered via oral gavage to pregnant female Harlan Sprague Dawley rats (n=10 per group) from gestational day (GD) 6 to GD 20. A number of endpoints were evaluated in dams and offspring. Endpoints evaluated in maternal animals were survival, clinical observations, body weights, food consumption, gravid uterus weight, and postmortem observations on GD 21 (gross visceral examination, corpora lutea, implants, and embryo/fetal mortality). Endpoints evaluated in offspring were fetal sex, weight, external abnormalities, and placental appearance. Because dams given the top dose of 900 mg/kg/day showed overt clinical signs of toxicity, that group was terminated early. Three dams in the 600 mg/kg/day group were also terminated early for the same reason. The remaining animals in the 600 mg/kg/day group showed decreased fetal weight and increased numbers of dead fetuses and resorptions (post-implantation pregnancy loss). The 300 mg/kg/day group showed decreased fetal weight, and the 150 mg/kg/day group showed slight fetal weight changes. No dose groups showed any increase in gross external fetal malformations. The results from this range-finding study indicate that the increased post-implantation pregnancy loss occurred at doses that induced significant maternal toxicity. Such significant maternal toxicity from chemical exposure often results in embryo-fetal toxicity, and effects on the fetus in these situations are usually considered non-specific, and secondary to maternal toxicity. Maternal toxicity in this study occurred at generally similar doses as reported in a 28-day toxicity study by the Eastman Kodak Company, which was the basis for the drinking water advisory level of 1 part per million set by the Centers for Disease Control and Prevention/Agency for Toxic Substances and Disease Registry.|NTP conducted a 5-day study in rats to evaluate the ability of three of the chemicals spilled into the West Virginia Elk River to cause chromosomal damage. These chemicals were 4-methylcyclohexanemethanol (MCHM), propylene glycol phenyl ether (PPH), and crude MCHM, a commercial mixture containing more than 70 percent MCHM along with lesser concentrations of other spill chemicals. Each chemical was mixed in corn oil and administered orally once daily for five days to separate groups of male rats at the following doses: Crude MCHM 0, 0.1, 1, 10, 100, 300, 500 mg/kg; MCHM pure 0, 0.1, 1, 10, 100, 300, 500 mg/kg, propylene glycol phenyl ether (PPH) 0, 1, 10, 100, 500, 1000 mg/kg (6 rats per dose level). Blood samples were obtained from the rats 24 hours after the fifth treatment, and the frequency of micronucleated red blood cells was measured using standard procedures. The results for all three chemicals were negative; none of these chemicals increased the frequency of micronucleated red blood cells in male rats after oral administration for five days.|The National Toxicology Program (NTP) evaluated the toxicity of six chemicals that were spilled into the West Virginia Elk River, four structurally related chemicals, and two chemical mixtures to the nematode roundworm Caenorhabditis elegans (C. elegans). These assays evaluated effects on growth and development, feeding, and reproduction at different developmental stages in C. elegans lifecycle. NTP found that none of the chemicals affected growth and development, feeding, or reproduction of C. elegans. The chemicals tested included the primary chemical in the spilled liquid 4-methylcyclohexanemethanol (MCHM); five other minor components of the spilled liquid namely dipropylene glycol ether (DiPPH), propylene glycol phenyl ether (PPH), 1,4-cyclohexanediemethanol, dimethyl 1,4-cyclohexanedicarboxylate, and 4-methoxymethylcyclohexanemethanol; four chemicals related in structure to MCHM or PPH; a commercial mixture crude MCHM containing primarily MCHM and smaller amounts of other chemicals; and a proprietary commercial mixture (DOWANOL DiPPh) containing different forms of DiPPH. ...The 12 chemicals tested in the C. elegans assays were added to the liquid where the C. elegans were living and tested at four concentrations (50, 75, 100, and 200 uM). In the case of MCHM, the four molar concentrations correspond to 6.4, 9.6, 12.8, and 25.6 ppm. Across the concentrations tested, there were no effects of the chemicals on C. elegans with regard to growth and development, feeding, or reproduction. No physical abnormalities between treated and untreated nematodes were observed during examination of nematodes by microscopy in any of the C. elegans assays.|Rashes and skin irritation were among the health effects reported by households following the chemical spill into the Elk River in West Virginia. The NTP conducted tests in mice to evaluate the potential for 4-methylcyclohexanemethanol (MCHM) and crude MCHM to cause dermal (skin) irritation and/or skin sensitization (hypersensitivity; i.e., allergic response) and to identify the concentrations at which such effects occurred. Dermal irritation results when a chemical causes localized skin inflammation by directly damaging cells. Skin sensitization results when a specific, structural component of a chemical causes changes in the immune system leading to an allergic response in the skin. In these studies, MCHM and crude MCHM were each diluted in a mixture of acetone and olive oil ...and applied to the ears of mice on study days 1, 2, and 3. The sample size was five mice per dose group. The mice were rested on days 4 and 5. On day 6, ear swelling at the site of application was assessed to determine any irritancy related effects. The proliferation (increase in number) of immune cells in the lymph nodes near the application site was measured to assess whether the exposure to either chemical caused skin sensitization by stimulating an allergic response. A second dermal irritancy and hypersensitivity study was performed on crude MCHM using different concentrations to verify the findings of the first study. Treatment of mice with 20 percent or 50 percent MCHM resulted in an increase in ear thickness that was indicative of mild skin irritation. MCHM did not cause increased proliferation of immune cells, indicating that it did not cause hypersensitivity. These results are consistent with toxicity information from previous studies by the Eastman Chemical Company. In the first study of crude MCHM, mice treated with up to 80 percent of the chemical mixture showed minimal evidence of dermal irritation. However, as the concentration of crude MCHM increased, there was an increase in the proliferation of immune cells in the lymph nodes closest to the site of application in the mice. This increase in immune cells indicates that crude MCHM produced skin sensitization at concentrations greater than or equal to 20 percent. In the second study of crude MCHM, mild dermal irritation was observed at the site of application at the highest concentration tested and skin sensitization was observed at concentrations of 50 percent and higher. In these studies, crude MCHM is considered a mild skin irritant, and this finding is consistent with previous studies by the Eastman Chemical Company. Importantly, these data indicate that crude MCHM induces hypersensitivity at concentrations lower than those that cause dermal irritancy. The hypersensitivity findings reported here are inconsistent with results from a previous study by the Eastman Chemical Company using a different model system that found crude MCHM did not produce skin sensitization. The reasons for this inconsistency are not currently known, but may relate to the use of different methods and a different formulation of crude MCHM.|For more National Toxicology Program Studies (Complete) data for 4-Methylcyclohexanemethanol (8 total), please visit the HSDB record page.
4-Methylcyclohexanemethanol's production and use as a mineral frother(1), reagent(2), and as a byproduct in the production of dimethyl hexahydroterephthalate(3) may result in its release to the environment through various waste streams(SRC).[(1) US EPA; Non-Confidential 2006 Inventory Update Reporting. National Chemical Information. Cyclohexanemethanol, 4-methyl- (34885-03-5). Available from, as of Jan 10, 2014: http://cfpub.epa.gov/iursearch/index.cfm (2) Reagent
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 34(SRC), determined from a structure estimation method(2), indicates that 4-methylcyclohexanemethanol is expected to have very high mobility in soil(SRC). Volatilization of 4-methylcyclohexanemethanol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.4X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 4-Methylcyclohexanemethanol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.8X10-2 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2014). Utilizing the modified Sturm test, 53% biodegradation was obtained in 4 weeks(4) indicating that biodegradation is not an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 34(SRC), determined from a structure estimation method(2), indicates that 4-methylcyclohexanemethanol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 6.4X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 7 and 51 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 22(SRC), from an estimated log Kow of 2.55(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the modified Sturm test, 53% biodegradation was obtained in 4 weeks(6) indicating that biodegradation is not an important environmental fate process in water(SRC).|AQAUTIC FATE: A dispersion-advection model was used to simulate the Elk river chemical spill 2014. The numerical and analytical solutions were used to predict the concentrations of 4-methylcyclohexane methanol (MCHM) at the water treatment plants located along the Elk and Kanawha rivers. The results are of similar magnitude as measured concentrations although a time-lag was found between modeled and measured plume arrival likely due to accumulation of systematic errors. Considering MCHM guidelines for drinking water, the spill represented a serious health threat through the water up taken by the treatment plant located on the Elk river and it also constituted a risk of contamination for the drinking water produced by treatment plants located on the Kanawha river|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-methylcyclohexanemethanol, which has an estimated vapor pressure of 5.8X10-2 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 4-methylcyclohexanemethanol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1 day(SRC), calculated from its rate constant of 1.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 4-Methylcyclohexanemethanol does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of 4-methylcyclohexanemethanol with photochemically-produced hydroxyl radicals has been estimated as 1.7X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1 day at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 4-Methylcyclohexanemethanol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 4-Methylcyclohexanemethanol does not contain chromophores that absorb at wavelengths >290 nm(2) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 22 was calculated in fish for 4-methylcyclohexanemethanol(SRC), using an estimated log Kow of 2.55(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of 4-methylcyclohexanemethanol can be estimated to be 34(SRC). According to a classification scheme(2), this estimated Koc value suggests that 4-methylcyclohexanemethanol is expected to have very high mobility in soil.|4-Methyl cyclohexane methanol (MCHM) is a flotation reagent often used in fine coal beneficiation and notably involved in the January 9, 2014 Elk River chemical spill in Charleston, WV. This study investigates the mechanisms controlling the transport and fate of MCHM in coal beneficiation plants and surrounding environments. Processes such as volatilization, sorption, and leaching were evaluated through laboratory batch and column experiments. The results indicate volatilization and sorption are important mechanisms which influence the removal of MCHM from water, with sorption being the most significant removal mechanism over short time scales (<1 hr). Additionally, leaching experiments show both coal and tailings have high affinity for MCHM, and this reagent does not desorb readily. Overall, the results from these experiments indicate that MCHM is either volatilized or sorbed during coal beneficiation, and it is not likely to transport out of coal beneficiation plant. Thus, use of MCHM in coal beneficiation plant is not likely to pose threat to either surface or groundwater under normal operating conditions.
The Henry's Law constant for 4-methylcyclohexanemethanol is estimated as 6.4X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 4-methylcyclohexanemethanol is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 7 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 51 days(SRC). 4-Methylcyclohexanemethanol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.8X10-2 mm Hg(SRC), determined from a fragment constant method(3).|4-Methyl cyclohexane methanol (MCHM) is a flotation reagent often used in fine coal beneficiation and notably involved in the January 9, 2014 Elk River chemical spill in Charleston, WV. This study investigates the mechanisms controlling the transport and fate of MCHM in coal beneficiation plants and surrounding environments. Processes such as volatilization, sorption, and leaching were evaluated through laboratory batch and column experiments. The results indicate volatilization and sorption are important mechanisms which influence the removal of MCHM from water, with sorption being the most significant removal mechanism over short time scales (<1 hr). Additionally, leaching experiments show both coal and tailings have high affinity for MCHM, and this reagent does not desorb readily. Overall, the results from these experiments indicate that MCHM is either volatilized or sorbed during coal beneficiation, and it is not likely to transport out of coal beneficiation plant. Thus, use of MCHM in coal beneficiation plant is not likely to pose threat to either surface or groundwater under normal operating conditions.
Occupational exposure to 4-methylcyclohexanemethanol may occur through inhalation and dermal contact with this compound at workplaces where 4-methylcyclohexanemethanol is produced or used. Limited population exposure may occur via ingestion of and dermal contact with contaminated water in the vicinity of a spill site. (SRC)
Drug Information
This study reports timely and original results of the mechanistic toxicity assessment of 4-MCHM and its metabolites via a newly developed quantitative toxicogenomics approach, employing proteomics analysis in yeast cells and transcriptional analysis in human cells. These results suggested that, although 4-MCHM is considered only moderately toxic based on the previous limited acute toxicity evaluation, 4-MCHM metabolites were likely more toxic than 4-MCHM in both yeast and human cells, with different toxicity profiles and potential mechanisms. In the yeast library, 4-MCHM mainly induced chemical stress related to transmembrane transport and transporter activity, while 4-MCHM metabolites of S9 mainly induced oxidative stress related to antioxidant activity and oxidoreductase activity.
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
/SIGNS AND SYMPTOMS/ Symptoms of 4-methylcyclohexane methanol include: Nausea, Vomiting, Dizziness, Headaches (ranging in severity), Diarrhea, Reddened skin, Itching, Rashes.|/CASE REPORTS/ In the days immediately following January 9, 2014, the West Virginia Poison Center received calls from over 1,900 patients reporting chemical exposures related to the drinking water. Most reported symptoms included mild rashes and reddened skin from dermal exposure, or GI distress (nausea, vomiting and/or diarrhea) from ingesting contaminated water. The symptoms tended to be mild and self-limiting.|/CASE REPORTS/ Hospitals were asked to release records for people who went to the /Emergency Department/ ED between January 9 and 23, 2014, and reported illness related to the chemical spill. A total of 584 records were released ... for review... 369 records were included in the final analysis; these records were for patients who had symptoms and reported they were exposed to the water... 13 (3.5%) of 369 persons were hospitalized. People who were admitted had chronic illnesses such as kidney, liver or lung disease. 356 (96.5%) of 369 persons were treated in the ED and released. Some treatments included IV fluids and/or medications for nausea or itching. The most common way people were exposed to the water was bathing, showering, washing hands, or other skin contact... The most common symptoms reported were nausea, rash, vomiting, abdominal pain, and diarrhea. Results of laboratory tests done in the ED did not indicate any people had new kidney or liver damage. People who reported that they swallowed contaminated water or food were more likely to report gastrointestinal symptoms such as nausea, vomiting, and diarrhea. People who reported skin contact with contaminated water were more likely to report redness or itching of the skin. ...Symptoms associated with exposure to low levels of MCHM in this public water system appeared to be mild and resolved with no or minimal treatment, such as IV fluids after episodes of vomiting or diarrhea and/or medications to relieve nausea or itching. Most people who reported illness associated with Elk River chemical spill were treated for their symptoms and released. Common symptoms included nausea, vomiting, diarrhea, skin rash, itching, headache, sore throat, and cough. These symptoms are consistent with known health effects of MCHM and with data reported by West Virginia Poison Center. It was possible that the symptoms reported to be caused by exposure to MCHM could have been caused by other mild clinical illness such as colds or flu or other viral infections. There are no laboratory tests or combination of signs and symptoms that can reliably distinguish mild illness caused by exposure to MCHM from /other/ mild illness. These data cannot prove that MCHM caused the reported symptoms; however, these data are consistent with what is known about MCHM from animal studies.|/GENOTOXICITY/ With human A549 cells, 4-MCHM mainly induced DNA damage-related biomarkers, which indicates that 4-MCHM is related to genotoxicity due to its DNA damage effect on human cells and therefore warrants further chronic carcinogenesis evaluation.
4-MCHM compound
4-Methylcyclohexanemethanol Use and Manufacturing
Solids separation agents
Coal flotation
Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#8162]|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Cyclohexanemethanol, 4-methyl-. Aggregated National Production Volume: 1 to < 10 million pounds.|Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Cyclohexanemethanol, 4-methyl-. National Production Volume: Withheld.
Flottec FX-140-04 Frother /Mixture of 10-20 weight % of 4-Methylcyclohexanemethanol with other alcohols/|Crude MCHM (68-89% 4-methylcyclohexanemethanol; 4-22% 4-(methoxymethyl)cyclohexanemethanol; 4-10% water; 5% methyl 4-methylcyclohexanecarboxylate; 1% dimethyl 1,4-cyclohexanedicarboxylate; 1% methanol; 1-2% 1,4-cyclohexanedimethanol).
All other basic organic chemical manufacturing|Cyclohexanemethanol, 4-methyl-: ACTIVE|4-methylcyclohexanemethanol (MCHM) is a chemical used to process coal. MCHM does not explode or catch fire. As a class of organic alcohols, it has an obvious odor and is reported to smell like licorice.|/Byproduct in the production of/ dimethyl hexahydroterephthalate.
During January 2014, an industrial solvent contaminated West Virginias Elk River and 15% of the state populations tap water. A rapid in-home survey and water testing was conducted 2 weeks following the spill to understand resident perceptions, tap water chemical levels, and premise plumbing flushing effectiveness. Water odors were detected in all 10 homes sampled before and after premise plumbing flushing. Survey and medical data indicated flushing caused adverse health impacts. Bench-scale experiments and physiochemical property predictions showed flushing promoted chemical volatilization, and contaminants did not appreciably sorb into cross-linked polyethylene (PEX) pipe. Flushing reduced tap water 4-methylcyclohexanemethanol (4-MCHM) concentrations within some but not all homes. 4-MCHM was detected at unflushed (<10 to 420 ug/L) and flushed plumbing systems (<10 to 96 ug/L) and sometimes concentrations differed among faucets within each home. All waters contained less 4-MCHM than the 1000 ug/L Centers for Disease Control drinking water limit, but one home exceeded the 120 ug/L drinking water limit established by independent toxicologists. Nearly all households refused to resume water use activities after flushing because of water safety concerns. Science based flushing protocols should be developed to expedite recovery, minimize health impacts, and reduce concentrations in homes when future events occur.|A heated purge-and-trap gas chromatography/mass spectrometry method was used to determine the cis- and trans-isomers of (4-methylcyclohexyl)methanol (4-MCHM), the reported major component of the Crude MCHM/Dowanol PPh glycol ether material spilled into the Elk River upriver from Charleston, West Virginia, on January 9, 2014. The trans-isomer eluted first and method detection limits were 0.16-ug L-1trans-, 0.28-ug L-1cis-, and 0.4-ug L-1 Total (total response of isomers) 4-MCHM. Estimated concentrations in the spill source material were 491-g L-1trans- and 277-g L-1cis-4-MCHM, the sum constituting 84% of the source material assuming its density equaled 4-MCHM. Elk River samples collected < or = 3.2 km downriver from the spill on January 15 had low (< or =2.9 ug L-1 Total) 4-MCHM concentrations, whereas the isomers were not detected in samples collected 2 d earlier at the same sites. Similar 4-MCHM concentrations (range 4.2-5.5 ug L-1 Total) occurred for samples of the Ohio River at Louisville, Kentucky, on January 17, ~630 km downriver from the spill. Total 4-MCHM concentrations in Charleston, WV, office tap water decreased from 129 ug L-1 on January 27 to 2.2 ug L-1 on February 3, but remained detectable in tap samples through final collection on February 25 indicating some persistence of 4-MCHM within the water distribution system. One isomer of methyl 4-methylcyclohexanecarboxylate was detected in all Ohio River and tap water samples, and both isomers were detected in the source material spilled.|Application of gas chromatography with mass spectrometric and human olfactory sniffer detectors reveals the nature of odorous chemicals from an industrial chemical spill. Crude 4-methylcyclohexane methanol (4-MCHM) spilled in a river and then contaminated drinking water and air for over 300,000 consumers living in West Virginia. Olfactory gas chromatography allows investigators to independently measure the odor of each chemical component in a mixture. Crude 4-MCHM is comprised of several major cyclohexane components, four of which have distinct isomer pairs. The cis- and trans-4-MCHM isomers are the only components to have distinct odors at the concentrations used in this study. The trans-4-MCHM is the dominant odorant with descriptors of licorice and sweet. Trans-4-MCHM has an air odor threshold concentration of 0.060 ppb-v (95% CI: 0.040 - 0.091). The odor threshold concentrations are not influenced by gender or age, but are lower by a factor of 5 for individuals with prior exposure compared to naive subjects. Individual trans-4-MCHM odor threshold concentrations vary by more than a factor of 100. The cis-4-MCHM isomer has approximately a 2000-fold higher odor threshold concentration, different descriptors, and an even wider individual response range.
Computed Properties
Molecular Weight:128.21
XLogP3:2.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:128.120115130
Monoisotopic Mass:128.120115130
Topological Polar Surface Area:20.2
Heavy Atom Count:9
Complexity:72.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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